Biodihydroxylation of substituted quinolines and isoquinolines by recombinant whole-cell mediated biotransformations. Issue 46 (17th November 2016)

• Record Type: Journal Article
• Authors: Zia, Muhammad Farooq; Vasko, Ágnes G.; Riedl, Zsuzsanna; Hametner, Christian; Hajós, György; Mereiter, Kurt; Mihovilovic, Marko D.
• Is Part Of: Tetrahedron. Volume 72:Issue 46(2016)
• Page Start: 7348
• Page End: 7355
• Publication Date: 2016-11-17
• Subjects: Dioxygenases -- Biocatalysis -- Asymmetric synthesis -- Chemoenzymatic synthesis -- cis-Dihydrodiols; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.06.077
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The recombinant whole-cell mediated biooxygenation of various quinolines and isoquinolines was investigated employing three different dioxygenases of bacterial origin. Substrate screening focused on the biotransformation of cyano-substituted azaarenes, in particular. Efficiently accepted substrates were submitted to scale-up of the enzyme mediated reaction to preparative scale. The regio- and stereoselectivity of the obtained metabolites was established by NMR and X-ray diffraction after appropriate derivatization. Graphical abstract: